


How Dean 'Got His Man' (In Five Easy Steps)

by ahrent



Category: Supernatural
Genre: Dean is ridiculous, High School AU, Human AU, M/M, On request, Valentine's Day, cas is oblivious
Language: English
Status: Completed
Published: 2014-02-14
Updated: 2014-02-14
Packaged: 2018-01-12 11:41:34
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,754
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1185818
Author URL: https://archiveofourown.org/users/ahrent/pseuds/ahrent
Summary: <blockquote class="userstuff">
              <p>So what if Dean hates Valentine's Day? It's apparently some magic pocket in time where anything and everything is possible, even gaining the attention and affection of one Castiel Novak. Dean is going for it.</p><p>Although maybe Seventeen Magazine isn't the place to get ideas.</p>
            </blockquote>





	How Dean 'Got His Man' (In Five Easy Steps)

**Author's Note:**

  * For [burninglikeabridge](https://archiveofourown.org/users/burninglikeabridge/gifts).



It's stupid, really. Dean doesn't even _like_ Valentine's Day. No, better yet, he doesn't even _care about_ Valentine's Day. He cares so little about Valentine's Day that he physically _could not care less_ about Valentine's Day. And so what if Castiel Novak, with his stupid hair and his stupid glasses and his stupid wrists and his frankly ridiculous hipbones, just _happens_ to be the reason Dean took that first, tentative step out of the closet. (When he tells the story later, it's not going to be so much a 'tentative step' as it's going to be a 'kicking down doors/taking no prisoners/playing air-guitar'-sort of coming out). That doesn't mean they're _meant to be_ or something as ridiculous as that. It just means that Cas is hot. And Dean is horny. That's nothing special. It certainly doesn't mean that Dean needs to care about _Valentine's Day_.

So it's really Sam's fault.

\--

It all starts when he's walking through the upstairs hallway to his room and Sam's door is open. Dean glances quickly into the room and then almost falls over as his upper body promptly stops moving but his legs don't get the memo. 

"…What are you doing?" He asks.

Sam looks up, "Oh, hey Dean. Just making some cards."

"Yeah, I can see that." Dean says, eyeing the mess on his brothers floor. "I'm kinda wondering why."

"It's Valentine's Day on Friday." Sam actually sounds insulted. Like, how _dare_ Dean insinuate that someone might, I don't know, _not_ make cards for Valentine's Day.

"And you care why?" 

Sam smiles down at his cards. "It's Valentine's Day, you're supposed to give out cards?"

"I don't know isn't it a little…" He trails off.

"What?" 

"Lame?"

"Dean!" Sam complains. 

"Fine, fine." Dean backs away from the doorway, "make your stupid cards. I don't care. I just don't see why you have to use so much glitter."

"The glitter is paramount!" Sam calls after him as he walks away.

What kind of freak keeps his bedroom door open anyway.

\--

Sunday night, Sam's making cards at the kitchen table.

"Aw, dude, come one, not where I _eat_!" Dean complains. Sam glares at him. It doesn't look very intimidating when he's holding a glue-stick in one hand and red paper in the other. Dean pushes some excess paper to the side and puts down his cereal bowl. "Who are you giving out cards to anyway, you're like twelve." He adds around a mouthful of milk.

"I'm fourteen!" 

The glare looks a little more intimidating when he's holding scissors, Dean will give him that much.

"How many are you even making? It's not for another five days." He comments.

"Yes, well," Sam looks down at his glittery paper with an air of indignation. "I have a test next week so I won't have time to make them then."

" _Nerd_." 

Sam throws his glue stick at Dean.

\--

 

Dean always thought that Valentine's Day was something you grew out of in middle school. Apparently, Lawrence High had not gotten that memo. 

He slams his tray down on the lunch table. "Why do people keep asking me out?" 

Jo glances up at him, and then resolutely ignores him. Gabriel is texting, and doesn't seem to be listening at all. Charlie at least answers. Charlie is probably his favorite.

"Because you're gorgeous, I didn't think this was news to you?"

Dean makes a frustrated sound, "no one's asked me out in _months_ , I didn't suddenly get more gorgeous did I?"

"Nope." Gabriel says, not looking up. Gabriel is definitely _not_ his favorite. 

"Did you _want_ people to ask you out?" Charlie asks pointedly.

Dean thinks about Cas, walking down the corridors wearing his large headphones, smiling to music Dean can't hear but really, really, wants to know about. "Not necessarily?" 

"There you go then, just say 'thanks but no thanks', and they'll give up again." She stuffs fries in her mouth.

"Give up _again_?"

She rolls her eyes, "please, anyone could tell that you're unavailable." As he starts to protest, she goes on, "you don't have to be in a relationship to be emotionally off the market. They moved on, to greener, less sad and hung-up pastures."

"They've obviously not moved on, I got asked out three times today. Three. Once by this one girl I have never seen before and who I'm pretty sure doesn't even _go here_."

"Wow, I thought I couldn't care less about this conversation," Jo says, "but I just did."

"It's Valentine's Day, El Deano." Gabriel says, still texting, "They get desperate for love and lower their standards. It's a wonderful time of the year."

"I don't think people lower their standards so much as they're more open to love." Charlie argues.

A guy from the art department is walking the length of the room, and as he does, drops flyers in varying shades of red and pink on the tables he passes. One lands directly in Dean's food. "Is Your Heart Lonely This Febrary?" bold letters scream up at him. He picks it up and waves it at the other's.

"And what the hell are these things? They're all over the corridors too, Valentine's Day was _not_ this big last year." He complains.

"Yes, it was." Charlie, Jo, _and_ Gabriel say. 

"You just had your hands too far up Lisa's blouse to notice." Jo adds.

"Oh. Right." Dean coughs. He'd forgotten about that particular disaster.

\--

Later, they're walking down the halls towards their lockers – Gabriel breaking away with a wave and an insult as they pass the junior lockers – and everywhere people are holding flyers, pointing at posters, talking in excited voices. Dean feels like stealing the football coach's whistle, getting everyone's attention, and screaming 'it's _monday_ , you have _four more days_ ' at everyone who will listen. 

They wrestle their way through the football team, standing around in their matching jackets like a herd of slightly unintelligent clones, to get to their lockers.

"Guys don't like these kinds of things to they?" Dean asks, eyeing the 'Chocolate of the Finest Quality, Here is Where It's At!'-poster sticking to his locker.

"What kinds of things?" Charlie asks.

"All the… flowers and the pink and the hearts and the chocolate. That crap."

"How are we _still_ on this?" Jo complains.

"Some guys do." Charlie provides unhelpfully.

"What kind of guys?" Dean asks. He knows for certain that he wouldn't be able to take a red, heart-shaped box of chocolates seriously any day of the year.

Charlie shrugs, "guys that aren't too busy making sure their tough-guy persona is in place to appreciate a nice gesture, I suppose."

Dean doesn't even bother addressing that painfully transparent insult. "I don't think guys like that exist outside of movies."

"I don't know," Jo says, and that is not a good voice, that is her gleeful 'let's make Dean Winchester suffer'-voice and that never brings good things to anyone that is Dean Winchester, "let's ask Cas." Dean's head whips around and sure enough, there's Cas, walking past them innocently, headphones over his head. "Hey, Cas!" Jo calls and grabs him.

Cas, when he realizes who suddenly pulled him aside, pulls his headphones off his head and says "Hello, Dean. Charlie, Jo." 

"Hi, Cas." Dean mutters and buries his head in his locker. Jo is a cruel, cruel woman and he will never forgive her for this.

"Hey, Cas, what's up?" Jo says, and doesn't wait for an answer, "so we were talking, and Dean here doesn't think that guys appreciate Valentines, what do you think?"

There is a pause and Dean glances out to see Cas gazing at him in that inscrutable, adorable manner of his.

"Valentines are a way to show appreciation, interest, and love, correct?" Cas asks.

"That's right!" Jo grins. Charlie's shoulders are shaking with suppressed laughter, and she keeps throwing Dean gleeful looks that make him want to reconsider whether or not she's his favorite after all.

"There is a universal want for these things, too, isn't there?" Cas continues.

"Right you are!" Jo claps him on the shoulder.

"Then everyone should benefit from this holiday." Cas concludes. "Though I don't really care for chocolate."

Of course, Dean thinks. Because Cas doesn't care about personas. He's too honest, and kind, and down to earth. _Of course_ Cas loves Valentine's Day.

"That's exactly what I've been saying." Jo nods. She's such a little liar. "Thanks, I'm sure you have to get to class now. I hope you get lots of Valentines this year." She waves him off.

"Goodbye, Dean." He says, and Dean only just doesn't hit his head on the roof of his locker.

"Yeah, bye Cas, have a good one." He waves, and then stops waving because it probably looks ridiculous. 

As soon as Cas is out of hearing range, Jo and Charlie collapse into laughter.

"You are cruel, _cruel_ people and because of that, I won't give you a ride home." He growls at them. They don't stop laughing.

He still gives them a ride home.

\--

Sam has laid out seven very glittery, very cheerful, very red-and-pink Valentine's Cards to dry on old newspapers on the kitchen table. Dean wonders how he thought he was going to explain that to their parents at dinnertime, or if they were just going to have to eat in the glitter.

So what if Cas likes Valentine's Day? That doesn't mean that Dean should make him a glittery, cheerful, red-and-pink card. It also doesn't mean that Cas would _want_ to get a card from Dean. They're friends. Good friends. So what if Dean feels like he's going into cardiac arrest every time Cas talks to him? That doesn't mean that Cas would even be remotely interested in going out with him.

He traces the outline of one of the less glittery cards with a finger.

Sam walks past and says in a sing-song voice, "You know, it's a great time to _catch someone's interest_ …"

Dean pulls his hand back and puts them both in his pockets. 

He think about Cas zoning out in class, Cas sitting outside the school with his headphones on, writing in the notebook he carries around everywhere, Cas saying 'Hello, Dean' and looking straight at him while Dean flushes and trips over his words and acts like a complete idiot. He thinks about what Charlie said about being open to love. He thinks about not having been asked out in nearly a year because apparently, everyone could see that he was pining, yes, _pining_ , for someone else. 

The thing is, he's been dancing around this whole Cas-thing for a _year_. It's embarrassing, really. He's never had this much trouble asking someone out before. He's never even _had_ trouble asking someone out at all. Dean of a year ago waltzed around the halls of Lawrence High, large as life, hooking up with girls in janitor's closets and having more dates than he could count. Then Cas just had to not so much waltz as trudge into his life with his stupid blue eyes and make him question _everything_. Damn Cas for making him realize that having his hands up Lisa Braeden's blouse simply won't make him happy. 

A year ago he would have thought any girl would be happy to have him. Now he has a hard time believing he could ever deserve Cas.

He knows that if he doesn't do this now, he might never. This is senior year. In June, they would all go off their separate ways and he might never see Cas again.

So what if Dean hates Valentine's Day. It's apparently some magic pocket in time where anything is possible. Maybe even getting the attention and affections of Castiel Novak. 

Sometimes he thinks Sam is a little too smart.

\--

 _Okay_ , he thinks, _if I'm going to do this. I'm going to need help_.

He imagines asking Jo for help, and immediately scraps that idea. Then he imagines asking Charlie for help, and realizes that she would without a doubt tell Jo and Gabriel, so he scraps that idea too. Then he imagines asking Gabriel for help, and feels a little ill. He considers Sam, and sees the years and years of endless teasing that would he ahead of him if he employed his fourteen year old brother to help him talk to the guy he likes. 

"Yeah, right." He mutters.

No, he's going to need to look elsewhere. They do have a computer in the house… which is his dad's. And in his dad's office. Right next to the living room. 

"I'm going to the library!" He calls to the house in general and heads for the front door. There is a momentary pause, then he hears Sam from upstairs:

" _What?_ "

"Hey, I study!" He hollers back up the stairs.

Sam comes thundering down the steps. "Not in the _library_ you don't." He says with a look of utter bewilderment on his face.

"Yeah, well maybe I need a change of scenery, don't be such a bitch about it." He counters as he pulls on his jacket.

Sam raises his hands in surrender. "Fine, sure, go to the library. Do you need directions?"

"Very funny." He slams the door behind him.

There is a muffled "Jerk!" from the other side.

\--

The library turns out to be a bad idea too.

 _Something must have gone very, very wrong with the world_ , he thinks, _for Dean Winchester to be sitting in a library, typing_ 'Valentine's Day gifts for guys' _into Google_. But there he is, sitting as close to the screen as he possibly can, trying to shield it from view with his body so that people won't see him scrolling through endless pages of chocolates, flowers, teddy bears, personalized love stories (please, they don't even _have_ a love story, that's what he is trying to _fix_ ), personalized cufflinks, and, holy fuck is that _edible underwear_? 

This is not working. These gifts are clearly intended for people already in happy relationships. With weird sex lives. Jesus Christ who wants someone to use their teeth _that close_ to their private parts?

He's starting to doubt his plan.

Dean has been head over heels ridiculously into Cas for a _year_. He doesn't just want to "show appreciation" he want's Cas to feel the same, dammit. Buying him a cute gift isn't going to achieve that.

He stares at the blinking cursor and the empty search-line and, in a moment of extreme weakness that he is going to deny for years to come, types _'how to get a guy to like me'_. In his defense, he really has no idea how to get a guy's attention. He knows how to get _girls'_ attention, and when they come on to him, there's a lot of twirling their hair around their fingers and laughing and touching his arm and pressing their breast against him and well… Dean doesn't think that would go so well if he tried it.

This is, of course, when the second half his English class walk through the doors of the library. He stares at them, stares at his screen, stares at them and, in a panic, clicks on the first link of the search results and presses 'print'.

The printer whirs slowly to life. 

"Come on, come on, come on–" he mutters.

The printer slowly starts spitting out a sheet of paper, inch by inch.

"Hey, Dean, is that you?" Benny calls.

Dean rips the paper out of the printer and gets the hell out of there.

It's not until he's safely home in his room that he finally looks at the sheet of paper in his hand. It's from Seventeen Magazine, and he doesn't even need to read the title of the article to know that that is bad. Then he does read the title of the article.

"How to get your man in 5 easy steps." 

He groans. 

\--

**Step 1: Dress to impress.**  
 _Men appreciate when you dress well. Wear something you like that you think he will like, and remember that there is nothing wrong with showing a little skin._

Something must have gone very, very wrong with the world for Dean Winchester to be standing in front of his closet on a Tuesday morning, comparing flannel shirts and actually feeling anxious about it. 

He gives it fifteen minutes of being completely unable to figure out whether Cas would like the green one or the red one best, before he gets angry, throws them both in the closet and leaves the house in only a T-shirt and his leather jacket. That step is stupid anyway, he decides. Cas doesn't care what Dean wears, _Dean_ doesn't even care what Dean wears. 'Showing a little skin' his ass.

When Sam asks if he's cold in just two layers, he just turns the music in the car up until he can't hear a word anyone's saying. 

**Step 2: Initiate contact.**  
 _You want to show your man that you're interesting and out-going. Get his attention and talk to him, try to be funny, but be careful not to seem desperate._

Dean stands with his head buried in his locker. This step doesn't seem so bad. He and Cas talk. Sometimes. There have been low key parties held by their mutual friends where Dean has been loose from a little beer where they have had great conversations about school, video games, their shared love of black and white movies, they'd even talked about recent events for fuck's sake. He can totally to this. 

Cas has French first thing on Tuesday mornings, and he will walk past Dean's locker to get to it. Dean does not know this because he is a creepy stalker, he knows this because they had once _talked about it_. Cas had mentioned that his teacher enjoyed giving them pop-quizzes, that's all.

There's Cas now, walking along with books under one arm, fiddling with his Walkman. As usual, Dean's heart does a stupid double take and he feels light-headed and a little clammy. To think he used to be so cool.

Dean shuts his locker and leans casually against it as Cas draws nearer.

"Hey, Cas, what's up– oh, you're still walking, okay, never mind, I'll just see you–"

He watches Cas' back as it disappears down the corridor. Then he bangs his head against his locker a couple of times. 

He _swears_ he used to be cool.

\--

He gives step two another try in Biology. 

Cas sits in front of him, and he swears, he _swears_ it's not stalker-y that his favorite thing about Biology is that he can stare at Cas' neck for an hour and a half without seeming like he's not paying attention. Biology is just really boring, alright. And Cas' neck is glorious. 

The first fifteen minutes of class he tries to think of a casual way to start talking while he also waits for the teacher to turn her back so he'll even have a _chance_ to talk. He's balancing his chair on two legs, keeping one eye on Ms. Wilkinson and one on the patch of flattened hair on Cas' head which looks like it's been pressed to a pillow for the entire night and not brushed out this morning. He'd press Cas into a pillow the entire–

Ms. Wilkinson turns her back and Dean puts his chair back in order and taps Cas on the shoulder before he loses his nerve. 

"Hey, can I borrow a pen– a pencil?" He asks, and why, _why_ does he ask to borrow a pen? Why does he go for the most obvious and juvenile thing he could possibly say right now? 

Cas neck twists and he already has a half-smile on his face when he catches Dean's eye.

"Dean." He says, and his name never sounds as good as when Cas says it. Then Cas looks at Dean's desk, and his brow furrows. "What's wrong with your pencil?"

Dean looks down at his own desk. Where his pen lies. He could pull up witness accounts and _they_ would swear he used to be cool.

"Oh." He says. "Nothing. Thanks anyway."

Cas smiles at him, and of course he doesn't laugh, because he's too good of a person to do that.

Damn him and his neck.

\--

**Step 3. Look your best.**  
 _Eye contact is the best way to show your man that your are interested. Always keep steady eye contact, it also shows that you're brave and ready for a challenge._

On Wednesday, Jo makes Cas sit with them at lunch. 

They haven't tried to push Dean at Cas like this in ages. It's like Valentine's drives people not only go-get-love but to force love upon every sad hung-up guy they know. Dean does not regret his decision to keep his 'five steps' a minimum of five steps away from his friends.

They plant Cas opposite Dean and give him matching shit-eating grins as they do. He glares at them and smiles at Cas. 

"So, Cas…" He starts, and fails to come up with any way to finish.

"Yes, Dean?"

"How was your weekend?" 

Cas has placed his ridiculously large headphones on the table between them. They're covered in stickers and Cas seems to have written something along the top of them but Dean can't make the words out. The stickers are haphazard and random; band names he doesn't recognize, jokes, what looks like a cat with wings. The text though, is small and neat, every letter carefully drawn out with a black pen. It's so _Cas_ that it's almost painful.

A voice that sounds suspiciously like Sam calls him lame in his head.

"Good, Dean. Uneventful." 

The same voice says 'eye contact, you ass' and he realizes that he is very intently staring at Cas' headphones. He looks up.

"Great. That's great." He says and looks Cas directly into the eyes. Cas gazes steadily back at him.

"How was yours?" Cas asks, and the guy's not blinking. At all.

"Yeah, good. Sam's making Valentine's Cards so I spent the weekend cleaning glitter off of, well, everything." _Be funny_ , the list had said. His eyes are getting dry, it really feels like he should blink now, but Cas isn't blinking.

Cas smiles a little wider, "I like Sam, he's very enthusiastic about AP Calculus."

"You know Sam?" How long is he supposed to look? The article hadn't been very clear, did he have to look until Cas looked away? What did it mean if he looked away first?

"I tutor two afternoons a week, he approached me about getting into some Junior-level courses."

Dean huffed a laugh, "that does not surprise me." Not Sam being unnecessarily enthusiastic about school _or_ Cas helping struggling students out in his free time. Now that he thought about it, Dean _is_ almost failing chemistry, maybe he could get some tutoring? Cas, wearing his glasses, leaning over Dean's desk, speaking into his ear, resting a hand against his neck– okay, no, not appropriate thinking at lunch. Focus.

Now his eyes are watering, this is not going as planned. 

"Do you have plans for Valentine's, Cas?" Charlie asks, and Cas looks away from Dean.

Dean furiously rubs his eyes. It takes a moment for Charlie's question to sink in, and then he's terrified. What if Cas has plans? What if he has a boyfriend? What if he has a _girlfriend_?

"No." Cas says, and Dean breathes a sigh of relief. Jo is leering at him. "Do you?"

Charlie grins, "you bet I do. It's going to be me, my Black Widow costume and my very own Wonder Woman."

"That's nice." Cas nods.

"Dean!" There's a blonde he doesn't know standing at their table, grinning at him and rocking back and forth on her feet.

"Uh. Hi?" He says.

"Hi!" She waves, "Wanna go out Friday?"

"Uh." He says again, and glances at Cas, who's looking on with a blank face, "thanks, but… sorry, I can't?"

"Oh, too bad, no worries though!" The girl waves again. "Bye!" She disappears as quickly as she appeared.

"Who was that?" Dean asks the table.

Jo and Charlie are too busy laughing to answer. Gabriel just grins and sucks on his lollipop. Cas is silently fiddling with his Walkman.

\--

**Step 4. Share his interests.**  
 _The easiest way to get your man to look at you in a new light is to show him that you have a lot in common. Make an effort to find out what he likes and show him that you care about what interest him._

Well. Step 1 through 3 had so far been completely useless. 

He crosses them in three hard strokes of his pen and looks at the fourth. He has his head far into his locker again, hiding the paper from view. He really does not want Gabriel to see and grab it out of his hand. That would be catastrophic. 

Shared interests though, that sounds promising.

They like video games. But there really isn't much he can do with that, short of inviting him over to play, and he really isn't ready to expose Cas to his parents. There's the same problem with movies, and there's no way he could pull off even pretending to be interested in Math or French. 

Cas does cross country running. Dean sees him all the time with the team, sweating and grinning and wearing _shorts_. Dean can't count how many times he's been distracted by those shorts, and the long, tight running pants he wears in the winter aren't bad either. Not. Bad. At all.

He always looks so happy when he's running. Dean only ever sees him unashamedly happy when he's running or when he's sitting somewhere, fiddling with his Walkman, gigantic headphones on his head. 

_Running_ , Dean thinks. _I could run. I could totally run._

\--

Dean cannot run. Repeat, Dean _cannot run_. 

He collapses against a tree and slides slowly to the ground. His lungs are tearing themselves apart and he is _dying_ , his muscles burn and his heart pounds in his ears and he _cannot run another step_. He should have known when the coach grinned gleefully at him and just _let_ him on the team. 

"Come back tomorrow, he said," Dean gasped, "join in on the run, he said. It'll be fun, he said."

He should have known when the coach paired him up with Cas for his first run so he wouldn't get lost, it was too easy, _way_ too easy. He _definitely_ should have known when he got to share a changing room with Cas, got to see those hipbones that had only been hinted at before, got to see Cas _shirtless_. Life just is not that kind. This was proof. Everything went well for twenty-four hours and now he's dying.

"Dean?" Cas asks, and that's just even better, he barely even sounded _winded_. "Are you okay?"

Dean waves a hand weakly, it really does feel as if his lungs are burning up.

"I told the coach this track was too long for a beginner." Cas sighed, "we can head back now."

"No, no, no," Dean manages to get out, "I'm fine, you go ahead, I'll catch up or… something." 

Cas looks down at him worriedly for a moment, then he promptly sits next to him on the ground. 

"We'll just wait until you catch your breath." He decides, and smiles at Dean. His hair is sticking to his forehead and he doesn't wear glasses when he runs so his eyes seem clearer than they usually do. He's a little flushed and has a smear of dirt on his cheek and Dean falls in love so fast and so hard it leaves him more winded than any running possibly could.

\--

He resigns from the cross country running team that same day, and the coach congratulates him on taking the record for shortest membership, at only 26 hours, ever. He doesn't mind really, because he's in love with Castiel Novak, and that is the best and worst thing in the world. 

Cas drives him home, since he had reluctantly given Jo permission to take Sam and the others in the Impala and he stupidly hadn't thought further than that. It's a strange feeling to not be driving for once. Not that he especially _wants_ to drive Cas' pick-up truck. 

"It has personality." Cas says.

"So does my car," Dean grins, "and it's not even falling apart."

"My car is fine." Cas states firmly, but he's smiling just a little. Dean can't stop looking at him.

Cas turns on the radio, and his smile changes as the music starts. This is the same smile he has when he's wearing his headphones; a fond, slightly absent smile that Dean can feel all the way down to his toes.

"Who's singing?" He asks.

Cas looks surprised, "This is Michael Burks, you've never heard him?"

Dean shakes his head. "This is blues, right? I mostly listen to rock."

Cas starts singing along quietly and Dean thinks he might just kiss him right then and there, steps be damned, but then, they are in a moving vehicle. 

"So is this what you have on that Walkman of yours?" He asks.

"Partly," Cas says, "there's also jazz, swing, and a little bit of rock'n'roll."

Dean smiles at that.

\--

Cas drops him off at the curb outside his house with a wave and a warm smile, and Dean hobbles inside, manages to avoid his parents and Sam and falls smile-first into his bed.

\--

**Step 5. The Grand Gesture.**  
 _By now your man is aware and interested, it is time to bring out the romance. The grand gesture is very personal. Think it through and make sure it's something your man will never forget. Good luck!_

He manages to force his stiff and unwilling muscles out of bed to have dinner. It's an awkward affair with Sam's suspicious calculating eyes trained on his face throughout, after which he makes his slow and aching way into John's office and the computer. He has a _plan_. A plan which he, for a change, actually has faith in. 

Grand gestures aren't his thing. He's fairly sure grand gestures aren't Cas' thing either. What he is aiming for is a gesture of moderate size, something that, if at all possible, will give him the chance to convince Cas that dating Dean is a good idea. A _great_ idea. Because Dean can totally be thoughtful.

Sam walks in just as he's, nervous and anxious and hopeful, folding a printed piece of paper and putting it in his pocket.

"So." Sam says, standing in the doorway with his arms crossed and a twinkle in his eye, "the _cross country team_."

"Don't even, Sam." Dean groans. "I learned my lesson, I'm in pain, I already quit, it's fine."

"The question isn't whether you've quit or not, it's why you joined in the first place."

Dean looks at his brother for a moment. "None of your business, Sammy." He gets out of the chair and limps past Sam towards the stairs. Sam follows.

"Really?" He asks gleefully, "not even if I happened to notice the big-ass _grin_ on your face when _Cas_ dropped you off today?"

Dean limps up the stairs. "Still none of your business." He mutters.

"Really?" Sam says again, "not even if I say that _Cas_ was talking about you yesterday?" 

Dean stops dead outside the door to his room, "he did? What did he say?"

The gigantic grin on Sam's face makes him realize just how that sounded.

"Shut up." He growls, goes into his room, and slams the door.

He hears Sam laughing from the other side.

\--

He manages to stay strong for about twenty minutes before he goes looking for Sam. He finds him lying on his bed, reading a book. 

"What did he say?" He mutters.

"I went to talk to him about Calculus, he asked how you were." Sam shrugs, without looking up form his book.

"Well, what did you say?" Dean prompts. 

"That you were fine! Really, Dean, just ask him out, it's getting boring to watch you pine all the time." He turns the page.

"Bitch." Dean mutters and goes back to his room.

"Jerk!" Sam calls after him.

"Boys, don't fight!" Mary calls from downstairs. 

\--

Friday morning, as they're on their way to pick up Jo, Sam keeps shooting him meaningful glances. After five minutes, Dean has had enough.

He turns down the music. "What? _What_ is it?" 

"Today's Valentine's Day." Sam says.

"I know, what of it?"

"Do you have something planned?"

He'd seen Sam carefully place each of his glittery cards in his backpack that morning. 

"None of your business." He says.

"That means yes." Sam leans back with a pleased smile.

\--

Dean's already leaning against Cas' locker when he shows up, and by then, it's almost a relief.

He's been standing there for twelve minutes already, and as every single one of them passed he panicked a little bit more. His hands are sweaty, and his hair is sweaty because he keeps running his fingers through it, and once every few minutes, he would take his jacket off and hang it off his arm just to change his mind and put it back on again. 

When Cas approaches, head down, headphones on and fiddling with his music, Dean has already considered every possible outcome of this conversation. There are many he likes; Cas pressing him up against his locker with his hands and hips and his mouth; Dean pressing _Cas_ up against the locker with _his_ hands and _his_ hips and _his_ mouth; Cas looking at him as if he loves him back; Cas looking at him as if there was a _possibility_ of him loving him back; Cas saying 'yes'; Cas saying 'maybe'. 

There are also several he does not like as much. Cas saying 'thanks, but no thanks', for example. Worse: Cas saying 'hell no'; Cas laughing at him; Cas punching him; Cas saying nothing. He tries to convince himself that Cas is too good of a person to do any of the more terrible one's. Dean's fairly sure that Cas will let him down easy, if that's the case. After all, he likes Dean. They're friends. 

He works himself up to a frankly ridiculous level of terrified anticipation, holding his folded peace of paper so hard his knuckles are turning white when Cas finally, _finally_ , strolls towards him, not looking up.

"Cas!" He calls before he looses his nerve. 

Cas looks up and, when he spots Dean, smiles, which makes Dean want to do a little dance. Or punch something. Anything to make the ridiculous butterflies in his stomach go away. Who knew all you had to do to understand the angst of all the teen romance dramas out there was to fall in love.

"Dean. Good morning." Cas says and places his headphones around his neck, his ridiculous neck. "How are your legs today?"

It takes a second for Dean to understand what he means. "Oh!" he says, "Meh, nothing I can't handle– well actually, that's a lie, it's really fucking painful."

Cas nods sympathetically, "I remember that from the first couple times I did it. It does get better, in case you want to give it another try?"

"Thanks, but running really isn't my thing."

Cas just smiles and moves to open his locker. Dean gets quickly out of the way. 

"So," he starts, and doesn't get any further. This is it. He's been building up to this for five days. Fuck, who's he kidding, for more than a year. _Now or never_ , Sam's voice sings in his head, _this is it_. He fiddles with the paper. "I found this place, last night, in Kansas City. I mean, I wasn't there or anything, I googled it. Well, not it, I stumbled on it while googling for _other_ things, you know, people do that. Anyway, it's this bar slash restaurant and they do live music sometimes–" Cas isn't looking in his locker anymore, but gazing at Dean over the top of the open door. His glasses have slid down his nose a little and before Dean can stop himself, he's reaching out and pushing them gently back up. Cas goes a little cross eyed trying to follow the movement. Dean snatches his hand back, "sorry, I just– never mind. Anyway. They do live music and tonight they're having a jazz-night and, well, you like music, I mean, you like jazz music. So if you're interested– I printed out the leaflet–" he thrusts it towards Cas. Is this what they meant about eye contact because he really, really cannot look away from Cas' eyes right now, "–if you think it sounds fun…" He trails off as Cas looks down at the paper.

"I've heard of this place." Cas says, and _yes, success_ , he sounds excited, "I've never been there before but it's supposed to have really good bands."

Dean feels hope bubbling in his stomach and just knows that this is a yes. He's standing with one foot in the door, he is _so_ close and he's been wanting this for a _year_ –

"Maybe Gabriel will go with me, he likes jazz." Cas muses and slams the metaphorical door in Dean's face. 

His stomach turns to lead and chest hurts. Why does his chest hurt? 

"Yeah." He hears himself saying, through the roaring in his head. "Uh, yeah, sure, Gabriel likes–" He runs his hand through his hair again. He's not sweating anymore. He just feels cold. "Cool, guess I'll see you later, then."

He walks away before Cas can try to catch his eye again.

\--

He ducks into the closest bathroom, scares the Freshman in there away with one look, and then kicks the side of a stall as hard as he can. 

\--

Valentine's Day isn't special. 

It is a regular goddamn Friday. There is no magical pocket in time where everything is possible. There isn't some sort of aphrodisiac in the air that makes everyone fall into each others arms and profess their undying love for each other. It's a Friday, and Dean has put himself on the line and it didn't work out and shit like that happens. He just wishes it had happened before he'd let himself fall unceremoniously in love. 

He also wishes it had happened on a day he wouldn't have to spend surrounded by heart shaped chocolate and people kissing and giving each other cards with cute little fucking love poems on them. That would have been nice.

"He's obviously not gay." Dean tells Jo and Charlie. No one is paying attention in English anyway, everyone is too busy giggling and gossiping and _kissing_. 

"I don't know, Dean, he seems pretty gay." Jo says, but at least she looks slightly sympathetic.

"I'm telling you, he didn't even realize I was asking him out." He mutters, leaning his chair as far back as possible without toppling over.

Jo and Charlie share a pitying look. He gets a little annoyed at that. He's heartbroken, not blind. 

The front legs of his chair thump back on the ground and he lays his head on the desk. Shit. He really is heartbroken. That's pathetic. 

"I'm sorry, Dean…" Charlie pats him on the head. "But, hey, you tried. After a year, that's pretty damn brave of you."

"You'll be fine, Winchester." Jo adds. "Plenty of gay fish in the sea, or something."

"I blame you." He said into the desk. "For spending the last year trying to get us together. It's your fault. All of it. And I will have my revenge."

"Whatever you say, Winchester." Jo pats him too.

\--

Neither Cas nor Gabriel are anywhere to be found at lunch. 

"You know, I don't care." Dean declares. "We're good friends, I like hanging out with him, we have things in common, that's enough for me. I don't need him to love me back, I'm not that desperate." 

Jo drops her fork. Charlie stares at him.

"What?" He asks.

"You're in love with him?" Jo asks.

"Fuck." Charlie says.

"I'll get over it." Dean says, "It's not like we're _meant to be_."

\--

He stops ten feet from his locker when he sees Cas leaning against it.

Jo and Charlie stop too, then they're patting him on the shoulders and leaving him with "It's been sweet, Winchester, but I'm gonna go be somewhere else." and "Yep, you're on your own for this one." 

He hisses "you're such _great friends_." at their retreating backs, but they either don't hear him, or choose to ignore him. 

With a deep breath, he heads towards Cas. 'It's not Cas' fault', he reminds himself, 'it's not Cas' fault, it's not Cas' fault, it's not Cas' fault–"

"Cas, hi." He says, and raises a hand. _Here comes the sweating again._

"Dean." Cas says, and he has his hands deep in how pockets, his headphones hang on his neck again –or still– and he looks almost nervous. 

"What's up?" Dean doesn't open his locker, but chooses instead to stand a respectable three and a half feet away, gripping his bag in one hand. He's fairly sure that his hands are shaking too badly for him to be able to unlock it now anyway, and he would like to not be obvious about it. If Cas is here to tell him that Dean's made him uncomfortable and that they can no longer be friends, he needs all the pride and self-confidence he can hang onto. Shit, what if he really is here to do that? Dean feels slightly ill.

"About earlier…" Cas trails off again, he's not looking at Dean, but rather at a point somewhere around his left shoulder. "Gabriel has, very firmly, informed me that I acted hastily."

There's silence. "Oh?" Dean prompts. If this is bad news, he wants it over with as quickly as humanly possible, and if this is good news, like his churning stomach and frantic heart are desperate for it to be, he'd like to _get_ to it, as quickly as humanly possible.

"He seems to be under the impression that you were inviting me to an evening at this restaurant, rather than informing me that it exists."

Dean doesn't know where to look. He scuffs his shoe against the floor and shrugs. Then he shrugs again, "Well." He says, "I was, I guess, but if you'd rather go with Gabriel or… someone else, then that's not a problem, I don't… have to go…" 

When he looks up, Cas meets his eyes. 

"You don't like Jazz." He says.

"I don't hate it." Dean says. "I mean, I don't _mind_ it, jazz can be nice."

"You wouldn't be going for the jazz." And it's so clearly not a question. Cas is looking at him so intently but Dean can't for the life of him figure out what that look _means_. Which of the frankly ridiculously number of scenarios he has in his head is that look leading towards? He knows what he wants it to be.

"No." He says, and neither of them are blinking, but for some reason, it's not as bad as last time.

"You'd be going for me."

"Yes." Dean nods, and that's a smile, that is definitely a smile on Cas' face and Dean is grinning too and why the fuck are they standing three and a half feet apart?

"Should we take your car?" Cas asks and Dean laughs. It's a loud, brash sound that doesn't go on for very long but by the end of it, Dean is standing very, very close to Cas.

Cas, who, with eyes shining with mirth, slides a hand onto Dean's neck and presses even closer. Dean grabs two handfuls of Cas' henley and breathes in; shampoo, laundry detergent, pine needles, burning ozone, salt water, Castiel.

He can feel Cas exhale against his lips.

"This is a date, right?" He murmurs, because even if all the evidence is pointing clearly towards his future happiness, he has to _hear_ it. "We're on the same page here?"

"Yes." Castiel says, and kisses him.

\--

When a freshman pokes Dean in the shoulder sometime later and says that the second bell is ringing and 'I know it's Valentine's Day and everything but you might want to get moving before you get detention', they know a lot more about each other's tongues than they did before.

Dean has almost all of his right arm underneath Cas' shirt, wound tight around his back, and his left hand is gripping one of those hipbones he's dreamt about for a _year_ and Cas has one hand firmly on the back on Dean's neck and the other even more firmly on his ass. 

They don't go to class that afternoon.

\--

At about 5:45 the next morning, Dean attempts to sneak into his house without waking anyone. His hair is on end, he has bags under his eyes, what feels like at least three hickeys and a few scratch marks, and an absolutely ridiculous grin on his face. He's fairly ready to crash into bed to try to sleep but really text Cas when he almost steps on Sam.

"Dude," Dean whisper-shouts, it doesn't even come out annoyed, Jesus, love's made a fool of him. "What the hell are you doing up?"

Sam has been sitting on the floor outside Dean's room, but he gets up when Dean tries to open the door around him.

"Hello, _Dean_." He whispers, so gleeful it hurts Dean's teeth. "Had a successful Valentine's _did we_?"

Dean goes into his room and kicks off his shoes. 

"Yes. I mean, I suppose. I mean yes. Why are you here, again?"

"Just wanted to make sure my big brother got home from his _date_ okay, at _six_ in the _morning_." Sam leans against the doorway, grinning widely.

"It was– you can– shut up, you're fourteen, how was _your_ Valentine's?" Dean deflects because he does not need to talk about his sex life with his little brother.

Sam doesn't answer.

"Sam?"

"It was weird." Sam mumbles.

"Why, what happened, did no one want you cards?"

"No, no, that wasn't the problem." Sam looks down at his socks, as if bewildered that he is even standing there. "It was just…"

"What?" Dean prompts.

"I got a Valentine's Card." Sam says, like it's the strangest thing to ever happen to him.

"So?" Dean asks.

"From Gabriel." 

Maybe Valentine's Day is a special sort of a day after all.

**Author's Note:**

> Written on request of burninglikeabridge, who wanted Dean to do something cute for Valentine's Day and for Cas to be oblivious. I hope you liked it!
> 
> Happy Valentine's Day everyone!


End file.
